A convenient synthesis of activated enantiomerically pure 2- ethynylaziridines

Tetrahedron Asymmetry

Volumn 9, Issue 22, 1998, Pages 3929-3933

  Ohno, Hiroaki ^a   Toda, Ayako ^a   Fujii, Nobutaka ^a   Ibuka, Toshiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHYNYLAZIRIDINE DERIVATIVE; ALDEHYDE DERIVATIVE; ALPHA AMINO ACID; AZIRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032573535     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00406-6     Document Type: Article

References (23)

1. For reviews on aziridines and their derivatives, see: (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984, Vol. 7, pp. 47-93. (b) Kasai, M.; Kono, M. Synlett 1992, 778. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedon: Asymmetry 1997, 8, 1693. (e) Rayner, C. M. Synlett 1997, 11. (f) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
2. For reviews on aziridines and their derivatives, see: (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984, Vol. 7, pp. 47-93. (b) Kasai, M.; Kono, M. Synlett 1992, 778. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedon: Asymmetry 1997, 8, 1693. (e) Rayner, C. M. Synlett 1997, 11. (f) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
3. For reviews on aziridines and their derivatives, see: (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984, Vol. 7, pp. 47-93. (b) Kasai, M.; Kono, M. Synlett 1992, 778. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedon: Asymmetry 1997, 8, 1693. (e) Rayner, C. M. Synlett 1997, 11. (f) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
4. For reviews on aziridines and their derivatives, see: (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984, Vol. 7, pp. 47-93. (b) Kasai, M.; Kono, M. Synlett 1992, 778. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedon: Asymmetry 1997, 8, 1693. (e) Rayner, C. M. Synlett 1997, 11. (f) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
5. For reviews on aziridines and their derivatives, see: (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984, Vol. 7, pp. 47-93. (b) Kasai, M.; Kono, M. Synlett 1992, 778. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedon: Asymmetry 1997, 8, 1693. (e) Rayner, C. M. Synlett 1997, 11. (f) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
6. For reviews on aziridines and their derivatives, see: (a) Padwa, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984, Vol. 7, pp. 47-93. (b) Kasai, M.; Kono, M. Synlett 1992, 778. (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedon: Asymmetry 1997, 8, 1693. (e) Rayner, C. M. Synlett 1997, 11. (f) Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
7. For recent syntheses of aziridines. see: Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1998, 39, 309. Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. 1998, 63, 4842. Church, N. J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1998, 1475. Atkinson, R. S.; Claxton, T. A.; Lochrie, I. S. T.; Ulukanli, S. Tetrahedron Lett. 1998, 39, 5113.
8. For recent syntheses of aziridines. see: Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1998, 39, 309. Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. 1998, 63, 4842. Church, N. J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1998, 1475. Atkinson, R. S.; Claxton, T. A.; Lochrie, I. S. T.; Ulukanli, S. Tetrahedron Lett. 1998, 39, 5113.
9. For recent syntheses of aziridines. see: Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1998, 39, 309. Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. 1998, 63, 4842. Church, N. J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1998, 1475. Atkinson, R. S.; Claxton, T. A.; Lochrie, I. S. T.; Ulukanli, S. Tetrahedron Lett. 1998, 39, 5113.
10. For recent syntheses of aziridines. see: Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1998, 39, 309. Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. 1998, 63, 4842. Church, N. J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1998, 1475. Atkinson, R. S.; Claxton, T. A.; Lochrie, I. S. T.; Ulukanli, S. Tetrahedron Lett. 1998, 39, 5113.
11. For recent syntheses of aziridines. see: Jeong, J. U.; Tao, B.; Sagasser, I.; Henniges, H.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 6844. Ando, T.; Minakata, S.; Ryu, I.; Komatsu, M. Tetrahedron Lett. 1998, 39, 309. Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. 1998, 63, 4842. Church, N. J.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 1998, 1475. Atkinson, R. S.; Claxton, T. A.; Lochrie, I. S. T.; Ulukanli, S. Tetrahedron Lett. 1998, 39, 5113.
12. Fugami, K.; Miura, K.; Morizawa, Y.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron 1989, 45, 3089.
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16. Coppola, G. M.; Schuster, H. F. In Asymmetric Synthesis; John Wiley & Sons: New York, 1987, pp. 1-363. Williams, R. M. In Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989, pp. 1-394. Hanessian, S.; Margarita, R.; Hall, A.; Luo, X. Tetrahedron Lett. 1998, 39, 5883. Hanessian, S.; Margarita, R. Tetrahedron Lett. 1998, 39, 5887.
17. Coppola, G. M.; Schuster, H. F. In Asymmetric Synthesis; John Wiley & Sons: New York, 1987, pp. 1-363. Williams, R. M. In Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989, pp. 1-394. Hanessian, S.; Margarita, R.; Hall, A.; Luo, X. Tetrahedron Lett. 1998, 39, 5883. Hanessian, S.; Margarita, R. Tetrahedron Lett. 1998, 39, 5887.
18. Coppola, G. M.; Schuster, H. F. In Asymmetric Synthesis; John Wiley & Sons: New York, 1987, pp. 1-363. Williams, R. M. In Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989, pp. 1-394. Hanessian, S.; Margarita, R.; Hall, A.; Luo, X. Tetrahedron Lett. 1998, 39, 5883. Hanessian, S.; Margarita, R. Tetrahedron Lett. 1998, 39, 5887.
19. Coppola, G. M.; Schuster, H. F. In Asymmetric Synthesis; John Wiley & Sons: New York, 1987, pp. 1-363. Williams, R. M. In Synthesis of Optically Active α-Amino Acids; Pergamon: Oxford, 1989, pp. 1-394. Hanessian, S.; Margarita, R.; Hall, A.; Luo, X. Tetrahedron Lett. 1998, 39, 5883. Hanessian, S.; Margarita, R. Tetrahedron Lett. 1998, 39, 5887.
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22. Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1, in press.
23. Enantiomeric purities of ethynylaziridines 13 and 14 have been determined by HPLC with a chiral stationary phase (Chiralcel OD and/or Chiralcel OJ) by comparison with their enantiomers (25 and 26) synthesized from D-valinol. Compounds 13 and 14 were found to be enantiomerically pure (ee >99%). (equation presented)